Ranking Every Episode of Mad Men

The first of the final seven episodes of Mad Men will premiere on Sunday, April 5th, bringing with it “The End of an Era,” as per AMC’s marketing campaign. They’re not overselling their product. Mad Men is one of the 21st century’s foundational shows. The heir apparent to The Sopranos, the show turned AMC into an industry powerhouse, ushered in the current wave of 1960s nostalgia and redefined our culture’s fashion and style. It’s also an amazing story, the Great American Novel figured as a seven season period drama.

To mark the occasion of Mad Men’s imminent conclusion, I recently rewatched the first six and a half seasons of the series. It was a rewarding experience, deepening my admiration for the show and undoubtedly further enriching my enjoyment of the final seven episodes. I liked some episodes more than I remember, certain missteps seemed harsher in retrospect, and the all-timers like “The Suitcase” only look better the older they get. Because all these episodes are fresh in my mind, and because the occasion to discuss Mad Men will never be better, I thought it’d be fun to rank every single episode of the series. I’ll revisit my ranking and post an updated version of the list once the final season has concluded.

The following is a ranking of every episode of Mad Men ever filmed, in ascending order.

There are no bad episodes of Mad Men, although the show did stumble on occasion and look more like a pretentious melodrama than a legitimately great show. There’s no better showcase for this than “Three Sundays,” which follows Don, Betty, and Peggy over the course of three consecutive sundays and their various personal mishaps. Mad Men was never good at dealing with religion and this episode’s lacklustre attempt to deal with Peggy’s guilt combined with an irritatingly earnest performance from Colin Hanks as Father Gill make for Mad Men’s darkest hour.

84. “The Benefactor” (Season 2, Episode 3)

Written by Matthew Weiner and Rick Cleveland; directed by Lesli Linka Glatter.

Bobbie Barrett was Don’s worst mistress. Neither sultry enough to convince the audience of her appeal nor smart enough to match him, she was a narrative ploy to alert Betty to Don’s infidelities. This episode, which introduces her and her irksome husband, Jimmy, hasn’t aged well because of these facts. Also, Mad Men is the last show where you want to hear Z-grade fat jokes, even if they’re coming from a character you’re meant to hate.

83. “To Have and to Hold” (Season 6, Episode 4)

Written by Erin Levy; directed by Michael Uppendahl.

This season six entry is where the show most resembled the melodrama of Megan’s soap opera. Harry Crane is sleeping with his secretary and fights with Joan to keep her hired; Megan gets a love scene on her soap opera, and her boss and co-star propose group sex with her and Don; Stan works in a sealed room on the Heinz Ketchup account. This episode contributed to season six’s erratic feel. At least we’ll always have the stupidity of the secret account name for Ketchup, “Project K.”

82. “Collaborators” (Season 6, Episode 3)

Written by Jonathan Igla and Matthew Weiner; directed by Jon Hamm.

Don’s affair with Sylvia Rosen was the most redundant part of Mad Men’s entire run. Perhaps that was the point, but that didn’t make it fun to watch him go through the same motions with his downstairs neighbour as he did with every other mistress he had, even if she’s played by Linda Cardellini. Also, Peggy taking advantage of Stan’s friendship in order to pitch for Heinz Ketchup was meant to be a cutting demonstration of “it’s not personal; it’s just business” but it comes off as pat. The most successful part of this episode is the dissolution of Pete and Trudy’s marriage, where Trudy lays down the law in a way only Alison Brie can accomplish.

81. “The Chrysanthemum and the Sword” (Season 4, Episode 5)

Written by Erin Levy; directed by Lesli Linka Glatter.

I bear no ill will towards this episode as there are parts I like, such as Roger’s protestations against courting Japanese clients and Don’s manipulation of CGC’s bid for Honda’s business. But the montage where SCDP schemes against CGC seems cute, and Mad Men should never look cute, as if the plot is a humourous counterpart to the plan in “Shut the Door. Have a Seat.” that was so thrilling. Also, the handling of Sally’s discovery of masturbation is plain awkward.

Mad Men Ladies Room

80. “Ladies Room” (Season 1, Episode 2)

Written by Matthew Weiner; directed by Alan Taylor.

This was the first real test of MadMen’s prowess as it was the first episode filmed after the series was greenlit, which took place a year after filming the pilot. As such, it’s an introduction to the ordinary rhythms that the show would follow in the early seasons and you can tell Matthew Weiner is still finding his legs. This entire episode can be summarized as being about Betty wanting to see a psychiatrist and Don thinking it’s a bad idea because he mistakenly thinks she’s happy. Mad Men often explored misogyny and the mores of the American nuclear family, but never quite as bluntly as this. Weiner was learning and he’d grow better at dealing with similar material in a more subtle way.

79. “For Those Who Think Young” (Season 2, Episode 1)

Written by Matthew Weiner; directed by Tim Hunter.

All I can say is that this episode is unmemorable. While I can remember specific details about all the other episodes of season two (even the episodes I don’t like as much), all I can recall about the episode is that Roger makes many comments about aging and being out of touch with youth. This is a table-setting episode, catching us up to where all the major characters are in 1962, but not giving us anything substantial on its own.

78. “Man with a Plan” (Season 6, Episode 7)

Written by Semi Chellas and Matthew Weiner; directed by John Slattery.

This episode has an overabundance of plot. It characterizes the messiness of season six. CGC moves into the SCDP offices. Joan gets sick and Bob helps her out, inadvertently saving his job in the process. Don drinks Ted under the table as an intimidation tactic. It’s juggling many plot threads, which are interesting, but it never focuses on one, which would allow us to learn anything new about the characters in the process. However, in the scenes between Don and Sylvia Rosen during their hotel room tryst, the show does clarify its attitudes towards sex and sex scenes: namely, that they are not sexy.

77. “Hands and Knees” (Season 4, Episode 10)

Written by Jonathan Abrahams and Matthew Weiner; directed by Lynn Shelton.

This is the episode where the request for a security clearance flags Don for the FBI and he spends the majority of the episode having panic attacks. This episode did deepen the interesting relationship between Don and Faye Miller, but considering the direction the relationship went in the following episodes, it seems like a lot of focus on a character who turned out to be relatively unimportant. The high point of the episode is Lane’s father visiting New York and clobbering him on the head with his walking stick. The abuse that poor man suffers on this show.

76. “Souvenir” (Season 3, Episode 8)

Written by Lisa Albert and Matthew Weiner; directed by Phil Abraham.

Don and Betty visit Rome on Connie Hilton’s dime. It’s meant to be the swan song of their marriage. The scene where Don and Betty roleplay in an Italian cafe is a nice little romantic moment, but the episode marks peak annoyance for Connie’s impositions on Don’s life. Also, I don’t know if they actually filmed the episode in Rome, but either way, the Italian setting is distractingly unconvincing.

75. “Tea Leaves” (Season 5, Episode 3)

Written by Erin Levy and Matthew Weiner; directed by Jon Hamm.

This is the introduction of Fat Betty into the series and a season and a half’s worth of TV recappers’ jokes on the subject. Betty started out the series as one of its most interesting characters but seasons four and five lost sight of that, allowing Don to turn her into a monster and only providing her with plotlines that marinated her spite. This episode makes clear the ever-present subtext that Betty is nothing more than a grown child, which is interesting, but nothing we didn’t already know.

74. “Blowing Smoke” (Season 4, Episode 12)

Written by Andre Jacquemetton & Maria Jacquemetton; directed by John Slattery.

In the wake of Lucky Strike pulling its account from SCDP, Don writes “The Letter,” the infamous ad in the New York Times that announces that his firm will never work with the tobacco industry again. “The Letter” had a huge influence over subsequent events in the series, but in this episode where it’s written and published, it’s not that important, merely another bold move on Don’s part to “change the conversation” and cement his place at the agency.

This episode is noteworthy for its use of voiceover, vocalizing Don’s journal entries in his bid to curb drinking and get a handle on his life. It’s full of stunning imagery like Don swimming at the New York Athletics Club, but the use of voiceover never felt natural for a series like Mad Men. The best part of the episode is Peggy’s elimination of Joey, the obnoxious freelance artist who preceded Stan.

Most of the episodes to follow are very good, including this one. Although this one brings back Father Gill and his irritating pleasantness, it uses the church plotline as a way to reflect on Peggy’s pressures at work, which reveals more about her character than delving into her lapsed Catholicism did. Also, although Jimmy Barrett is an irritating character, the scene where he tells off Don at a party for sleeping with his wife is a glorious moment of honesty. It reveals that even little shitheads like Jimmy understand that Don does loathsome things.

71. “Indian Summer” (Season 1, Episode 11)

Written by Tom Palmer and Matthew Weiner; directed by Tim Hunter.

In the midst of Roger’s repeat heart attacks, Cooper offers Don a partnership at Sterling Cooper. As well, Betty invites a traveling air conditioner salesman into the home, much to the ire of Don. This episode mostly sets up the final two episodes of the season, but it also brings us deeper into Betty’s mind and allows us the pleasure of Cooper’s dangling the reward of the partnership before Don, the hungry dog. He is the one man on the show who always saw Don for what he is and used Don to his advantage at every turn.

Mad Men The Fog

70. “The Fog” (Season 3, Episode 5)

Written by Kater Gordon; directed by Phil Abraham.

Betty gives birth to Gene as she becomes delirious, hallucinating about her dead father and mother. Mad Men didn’t do dream sequences often, so when they do show up, they’re entertaining but tonally off. The rest of the episode, however, is top notch, especially Don’s waiting room conversation with a prison guard expecting his first child. The man’s sincere farewell to Don as he goes off to greet his child for the first time, telling Don that he’s a good man, is heartbreaking.

Don’s philandering was apparent from the pilot episode, but as the first season progresses, the show makes clear that Roger goes even further than Don in this department. In this episode he talks Don into entertaining twin models in his office and ends up having a heart attack. Watching Roger Sterling go to town with his charm is always a pleasure and the sight of him suffering a heart attack juxtaposes that pleasure with some real sadness. It’s also an apt metaphor for his predilection to overdose on carnal appetites.

68. “The New Girl” (Season 2, Episode 5)

Written by Robin Veith; directed by Jennifer Getzinger.

This is the episode where Don and Bobbie Barrett get in a car crash and Peggy has to bail them out of jail. Although Bobbie was a dud of a mistress, this plotline reveals more about Don’s relationship to Peggy than it does about Bobbie. Finding out about what happened after Peggy disappeared to have a baby and Don’s involvement in it enriched their relationship to a level beyond mentor and protege. The episode also allows Bobbie some measure of wisdom when she gives Peggy advice about being a woman.

Mad Men is a stylistically bold show and as the series progresses, it gets bolder. This season three entry starts with both Don and Peggy in hotel rooms. Don is bloodied and Peggy’s in bed next to a mystery man. As the episode flashes back to the day before, we see how both Don and Peggy ended up where they did. This is another episode linking Don and Peggy, even though they don’t share a plotline in it. Don and Peggy may be brilliant at work, but they’re terrible at life choices. This episode hits home that fact.

66. “The Flood” (Season 6, Episode 5)

Written by Tom Smuts and Matthew Weiner; directed by Christopher Manley.

This is the episode where Martin Luther King Jr. gets shot and everyone goes into a panic. Mad Men often centres episodes around shattering historical events. This episode is its least successful iteration of that successful formula. It again has characters huddled in front of television sets, asking openly about the meaning of life when death comes so easily to great men, but it doesn’t shake you the way “The Grown-Ups” does. However, it’s still a strong episode, capturing the chaos of 1968 America and the feeling of disillusionment people must have felt. Also, it has Pete Campbell holding the moral ground against Harry Crane regarding MLK’s death, which is kind of like Mussolini berating Hitler, but it’s still a minor triumph for the character.

65. “Christmas Comes But Once a Year” (Season 4, Episode 2)

Written by Tracy McMillan and Matthew Weiner; directed by Michael Uppendahl.

Lee Garner Jr. pays a surprise visit to the SCDP Christmas party and everyone has a jolly time. Don sleeps with his secretary while in a drunken haze. This episode isn’t much for thematic substance, but it is a pleasure from start to finish. It’s worth watching if only for the hilarious sight of Pete and Trudy Campbell dancing in a conga line.

64. “Favors” (Season 6, Episode 11)

Written by Semi Chellas and Matthew Weiner; directed by Jennifer Getzinger.

This is a noteworthy episode for the scene where Sally Draper discovers her father having sex with Sylvia Rosen. It’s a crushing moment and a series low for the character. This one scene is shattering. The rest of the episode is par for the course for season six, dealing with the merger between SCDP and CGC and Don trying to get Sylvia’s son out of the Vietnam draft.

63. “Love Among the Ruins” (Season 3, Episode 2)

Written by Cathryn Humphris and Matthew Weiner; directed by Lesli Linka Glatter.

Grandpa Gene’s partner, Gloria, leaves him and Don agrees to have him come live with him and Betty. It’s one of the few times Don sacrifices anything for Betty’s happiness. As well, the Grandpa Gene storyline is much more poignant than I remembered it being, offering a thoughtful look at dementia and the conflicting wisdom and bigotry of old age.

62. “Red in the Face” (Season 1, Episode 7)

Written by Bridget Bedard; directed by Tim Hunter.

It’s clear that Roger is the closest person to Don at Sterling Cooper and this episode explores that relationship as Roger hits on Betty and Don humiliates Roger in front of clients. It’s another episode in season one that isn’t especially rich in subtext nor is it explosive in terms of plot, but it does show the degrees of shamelessness that both Roger and Don represent. They’d always mirror aspects of each other throughout the series and this episode clarified their relationship in a way that allowed for the subsequently richer relationship to develop between them.

61. “A Tale of Two Cities” (Season 6, Episode 10)

Written by Janet Leahy and Matthew Weiner; directed by John Slattery.

Don, Roger, and Harry take a trip to Los Angeles and Joan makes a move to become an accounts executive in her bid to land Avon. Season six exists in a haze of marijuana smoke and this episode took advantage of that better than most. Don’s hash trip embraces the trippiness of the late sixties while Danny Strong punching Roger in the nuts is enough of a recommendation. Season six and seven increasingly muddled up Joan as a character, but “A Tale of Two Cities” is one of the few moments where her motivations are clear and her resolve is admirable.

Mad Men Time Zones

60. “Time Zones” (Season 7, Episode 1)

Written by Matthew Weiner; directed by Scott Hornbacher.

Season premieres on Mad Men fluctuate between being table-setting episodes or movies in miniature. This one skirts between the two and its less successful for it, focusing on Don’s bi-coastal life post-SC&P, but also showing Ted and Pete’s acclimatization to Los Angeles, Joan’s jockeying for accounts, and Peggy’s frustrations with the son-of-a-bitch creative director, Lou Avery. Everything having to do with Don is very interesting, especially a hazy conversation he has with a woman (played by 90s star Neve Campbell) sitting next to him on a plane and his funneling of ad ideas through Freddy Rumsen. But the rest is merely getting us ready for the final run of episodes, which is necessary but had been done with more finesse at other times in the series’ run. At least it has that stunning shot of Jessica Paré getting out of the convertible.

59. “The Hobo Code” (Season 1, Episode 8)

Written by Chris Provenzano; directed by Phil Abraham.

This is the episode where Don learns how to read people from a hobo, in flashbacks that is. This episode is fundamental to understanding Don Draper as a character and how he got to where he is when the series begins. Aside from this plot thread, the episode is best remembered for Don’s comfortable dismantling of Midge’s beatnik friends. At few times in the series is Don more comfortable among the counterculture.

In the midst of Don and Betty’s separation, Grandpa Gene has a stroke and they go to visit, feigning to be a loving married couple for the sake of Betty’s relations. This is the first chapter in the saga of Grandpa Gene and it’s predictably awkward and poignant. The part where Gene mistakes Betty for her dead mother and makes a pass at her is painfully sad.

57. “The Monolith” (Season 7, Episode 4)

Written by Erin Levy; directed by Scott Hornbacher.

SC&P gets a computer and Michael Ginsberg starts to go insane. While this plotline wouldn’t pay off until the following episode, “The Monolith” does give us plenty of 2001: A Space Odyssey references, starting with the shot of the elevator door when Don returns to work after his absence. The episode also shows how close Don gets to blowing his chance at redemption. Despite his best intentions at cleaning himself up, the realization that he’s been reduced to writing taglines is enough to send him off the wagon. Freddy Rumsen is his godsend here, forcing him to pick himself up and swallow his pride. As well, “The Monolith” gives us Roger going to the commune to visit Margaret, which is a typical showcase for John Slattery, even though Margaret is the most annoying character to grace the series with her presence.

56. “The Beautiful Girls” (Season 4, Episode 9)

Written by Dahvi Waller and Matthew Weiner; directed by Michael Uppendahl.

As the title suggests, “The Beautiful Girls” is all about the show’s female characters. Joan hooks up with Roger after being mugged, a hookup that would ultimately produce her son Kevin. Peggy goes on a disastrous date with Abe. Miss Blankenship dies hilariously at her desk. And most importantly, Sally runs off to the office. It’s a strong episode overall, juggling how these women’s lives run differently than their male colleagues purely due to their sex, but the grace note for the episode is the first substantial appearance of Megan, where she catches Sally when she falls down running away from Don’s office. Watching the way Megan gracefully handles Sally’s fall and comforts her was enough to hook Don. It’s such a small moment but introduces Jessica Paré’s magnetic screen presence.

55. “Dark Shadows” (Season 5, Episode 9)

Written by Erin Levy; directed by Scott Hornbacher.

The worst parts of “Dark Shadows” are the scenes of Betty trying to poison Don and Megan’s marriage from a distance, dropping hints about Anna Draper to Sally and getting her to prod the newlyweds’ marriage. It’s another example of season five’s one major misstep, its handling of Betty. However, the rest of the episode is really strong, especially the parts following Don’s jealousy of Ginsberg’s talents and his torpedoing of his Sno Ball ad in favour of his inferior alternative.

54. “5G” (Season 1, Episode 5)

Written by Matthew Weiner; directed by Lesli Linka Glatter.

This was the first episode alerting us to the fact that Don Draper was fake in more than a metaphorical way. As Don’s brother, Adam Whitman, arrives in New York to force himself into Don’s life, Don pays him off. He fondly recalls his little brother but he can’t risk his new life for the sake of people from his past so he deals with Adam the only way he knows how: with money. In the first few episodes of Mad Men, Don Draper looks like the ideal man, despite his philandering and lying ways. “5G” gave us the first taste of his true patheticness.

53. “The Jet Set” (Season 2, Episode 11)

Written by Matthew Weiner; directed by Phil Abraham.

Many people are probably wondering why I don’t rank this episode higher. While I admit that Don’s first visit to California has glorious moments, I’m not entirely comfortable with the characterizations of the European nomads he gets in with. The episode works best as another reminder of how deftly Don Draper can reinvent himself. Also, Pete’s adamance that he get to sit at the hotel pool while making his business calls is hilarious.

52. “The Crash” (Season 6, Episode 8)

Written by Jason Grote and Matthew Weiner; directed by Michael Uppendahl.

This one played better on a first viewing when I didn’t know what I was in for. The drug-addled craziness of SCDP and CGC working on Chevy over the weekend while high on speed is full of golden moments, but the Don/Sylvia relationship, one I didn’t care for, draws too much of its focus. I no longer care about its narrative significance and purely enjoy it for the lunacy on display: Stan racing Cutler through the office, Don losing a whole day walking down the hall, Ken crashing a car when one of the Chevy executives masks his vision, and, best of all, Ken doing a tap dance in protestation.

51. “Wee Small Hours” (Season 3, Episode 9)

Written by Dahvi Waller and Matthew Weiner; directed by Scott Hornbacher.

Don pursues a relationship with Sally’s former teacher, Suzanne, and Betty pursues her fascination with Henry Francis. Both of these plot threads are interesting as they lead the two Drapers down the road to their eventual divorce, but this episode is most noteworthy for being Sal’s exit. The desperation on Sal’s face as he talks to Don about Lee Garner Jr. making advances on him and Don refusing to help him is heartbreaking. Sal’s final scene where he calls his wife to tell her he’ll be late for dinner, only to disappear into the woods with a group of fellow homosexuals only reinforces the heartbreak. It’s one of the few moments where the series clearly shows how the world can destroy a man.

Mad Men The Runaways

50. “The Runaways” (Season 7, Episode 5)

Written by David Iserson and Matthew Weiner; directed by Christopher Manley.

Anna Draper’s niece, Stephanie, makes an appearance in this episode, pregnant and in need of help. Don sends her to Megan’s, where she forces money on her and sends her on her way to Oakland before Don can come visit. Almost three seasons after Anna Draper’s death, this episode is a nice reminder that Don does have a few people he cares about in the world. Because she reminds him of Anna, Stephanie is one of those few people, and Megan using that small measure of kindness in Don to get back at him is dramatically crushing. However, this isn’t all the episode has to offer. It also has Ginsberg cutting off his nipple to stop the computer signals from destroying his mind, Jim Cutler and Lou Avery talking in the computer room like Dave Bowman and Frank Poole in 2001: A Space Odyssey, and, of course, Lou Avery’s pathetic cartoon, “Scout’s Honor.”

49. “The Color Blue” (Season 3, Episode 10)

Written by Kater Gordon and Matthew Weiner; directed by Michael Uppendahl.

“The Color Blue” sets up a lot of the big plot developments that’ll end season three with a bang, but it’s still very memorable in its own right. It’s full of great character expressions and facial reactions: Lane’s dejected look at learning that Sterling Cooper is being sold to McCann Erickson, adding depth to a character who would only become increasingly important; Betty’s face when looking upon the photos of Dick and Adam Whitman in Don’s shoebox; and best of all, Betty’s mental gymnastics at the 40th Anniversary Party for Sterling Cooper, watching her husband receive an award and realizing that she’s married to a man she doesn’t know.

This is one of those good time Mad Men episodes where the pleasures of the show are so great, you don’t care whether the episode is deep or not. Luckily, seeing as this is an episode of Mad Men, it boasts depth as well as entertainment. As Roger and Don fête Freddy Rumsen after they fire him for drunkenly pissing himself before an important pitch, we’re privy to the sight of these two powerful men drunkenly conquer New York City. That the episode also happens to have a heartfelt barside conversation between the two that ultimately causes Roger to divorce Mona is an indicator of its deftness of tone.

Don uses Peggy’s Rosemary’s Baby advertisement pitch to put a wedge between her and Ted and Pete uncovers Bob Benson’s secret. This episode is all about office relationships and the ways people use others’ secrets to their own advantage. The standout moment is Pete’s confrontation of Bob Benson, revealing that Bob is just another Don Draper, a con man who created a new identity to succeed in the world. That Pete choses not to fight him shows the character’s modest growth over the course of the show. He may be an asshole, but Pete understands when not to pick a fight he’ll lose. Also, Ken gets shot in the face by the Chevy executives, continuing the season’s hilarious mistreatment of our beloved accounts man.

46. “Out of Town” (Season 3, Episode 1)

Written by Matthew Weiner; directed by Phil Abraham.

Don and Sal go to Baltimore during a business trip and Don discovers that Sal is homosexual. That Don doesn’t use this information against Sal and that he’s more interested in the work at hand instead of his salacious discovery reveals a new facet of the character: he’s not interested in other people’s secrets. Sal was the show’s greatest loss. Episodes like this that give him a spotlight are a treat.

45. “Flight 1” (Season 2, Episode 2)

Written by Lisa Albert and Matthew Weiner; directed by Andrew Bernstein.

Pete Campbell is justifiably hated by viewers as he’s an irritable twerp, but he’s a great character. “Flight 1” adds to his already substantial depth by following his mourning (or lack thereof) after his father dies in a plane crash. The fact that Don is the first person he tells shows Pete’s already growing admiration and loyalty to his one-time nemesis. As well, it reveals Pete’s pathological predisposition toward pleasing others. Even in the time of great loss, he wants to do what others expect of him, which is cry and go into mourning, not what he feels, which is nothing.

44. “A Day’s Work” (Season 7, Episode 2)

Written by Jonathan Igla and Matthew Weiner; directed by Michael Uppendahl.

This episode thrives off irony. Sally discovers that Don is no longer working at SC&P. Pete lands a new client only to have Jim Cutler insist on running the prospect by their existing clients. Best of all, Peggy thinks that her secretary’s flowers are a gift from Ted for her, precipitating a hilarious secretary swap and scenes of passive aggression. Peggy is the show’s co-protagonist, the positive mirror of Don, but she’s still allowed to be foolish and proud and pigheaded, as this episode beautifully demonstrates.

43. “The Rejected” (Season 4, Episode 4)

Written by Keith Huff and Matthew Weiner; directed by John Slattery.

Pete episodes are always interesting even if they lack the narrative fireworks of season finales or Don episodes. Still, as interesting as Pete’s plotline is here, focusing on his loss of his father-in-law’s business due to a client conflict and the announcement of Trudy’s pregnancy, John Slattery’s directorial flourishes steal the show. The show’s best comic performer, Slattery also proves himself to have a keen eye for comedy. The simple shot of Lane popping his head around one side of the column in Pete’s office and then popping it around the other side when Pete calls him back to clarify something is beautiful filmmaking.

42. “Mystery Date” (Season 5, Episode 4)

Written by Victor Levin and Matthew Weiner; directed by Matt Shakman.

This episode is all about the darkness. As a serial killer lurks in the headlines, Peggy and Dawn are scared to head home from the office, Sally stays up with Grandma Pauline, and Don has a fever dream where he imagines himself killing an old flame. The episode’s grand histrionics are far from subtle, but they create a lasting impression, casting the entire episode in darkness and making this one of the most surreal episodes of the series’ entire run.

41. “Smoke Gets in Your Eyes” (Season 1, Episode 1)

Written by Matthew Weiner; directed by Alan Taylor.

As a pilot, this episode is aces. It establishes a fascinating protagonist, an appealing story world, and lays the groundwork for a whole season of conflict and intrigue. As an episode of Mad Men, it has to content itself to being very good, but far from the best. While the opening moments scored to Don Cherry’s “Band of Gold” still gives me goosebumps, the episode as a whole falls prey to the pilot problem, where all the characters are a little broader and the filmmaking flashier than what would come after. It makes sense as the show had to grab attention, but such outward displays of raciness, like the burlesque show that Pete goes to for his bachelor party, seem like a part of a different, HBO-lite show, not Mad Men. The one thing the episode gets very right, however, is Don Draper, a character who was beguiling from the first moment you saw the back of his head while he was scribbling on a napkin.

Mad Men The Better Half

40. “The Better Half” (Season 6, Episode 9)

Written by Erin Levy and Matthew Weiner; directed by Phil Abraham.

Season six was able to return Betty to being an interesting character after she had descended into the role of spiteful shrew. This episode, where Don and Betty hook up while attending Bobby’s summer camp, recaptures what made Betty so fascinating in the first season. It’s not for nothing that the episode marks the reappearance of Betty as thin and blonde, just like the woman we met at the ending of the pilot. Betty always looked the ideal housewife, beautiful and accommodating, but she had plenty of psychological depth beyond her infantilization and this episode took advantage of that. Also, this episode has Peggy stabbing Abe in the chest with a makeshift bayonet, which is priceless.

38-39. “A Little Kiss” (Season 5, Episodes 1 & 2)

Written by Matthew Weiner; directed by Jennifer Getzinger.

This episode is what I referred to before as a movie in miniature. It shows us Don and Megan’s marriage around a year into progress. The centrepiece is Megan’s surprise 40th birthday party for Don, which he predictably hates. However, it does gift the audience with the sumptuous sight of watching Jessica Paré coo “Zou Bisou Bisou” to Don while everyone else from the office watches on, and the viewer stares in awed silence. If “The Beautiful Girls” had an eye-catching introduction to Megan, this was the star-making showstopper.

37. “Christmas Waltz” (Season 5, Episode 10)

Written by Victor Levin and Matthew Weiner; directed by Michael Uppendahl.

Joan and Don aren’t characters who spend a lot of time together on the show. This episode corrected that, giving us a centrepiece where Don and Joan test drive a Jaguar and hang out in a bar, shooting the shit. It’s a pleasure as two of the show’s most magnetic stars are allowed to bounce off each other. Also, considering how Joan and Don’s relationship disappointingly developed in season six and seven, this episode is the last bright spot in a beautiful friendship that should have lasted longer.

36. “Marriage of Figaro” (Season 1, Episode 3)

Written by Tom Palmer; directed by Ed Bianchi.

The first two episodes of Mad Men were a good introduction to Sterling Cooper and the people who worked there, but this was the first episode to really cement the rhythm that would define the show. As Don courts Rachel Menken in and out of the boardroom, Betty prepares for Sally’s birthday party. The domestic scenes are the standout here, which was rarely the case on a show where the office reigned supreme. There are beautiful moments like Don putting together Sally’s playhouse, going back to the garage fridge for beer after beer, until he’s too drunk to finish the job and retreats inside to continue drinking, this time with other people. There’s also the great finish where he arrives back home after hours MIA, only to surprise Sally with a labrador retriever. If there’s one thing Don Draper has learned how to do, it’s buy people’s affection, especially the affection of family members.

Betty finally confronts Don with the truth about his past and he fesses up—to a point. Don Draper is never one for giving full truths, only half truths that avoid easy lies. Don’s weakness at the sight of his photographs gives Betty the upper hand in their relationship for the first time in forever. It’s an empowering moment for Betty, a character who rarely seemed in control of a situation. Also, there’s the classic ending where Don and Betty take the kids trick or treating and a neighbour recognizes the kids’ costumes before turning to Don and asking who he is. It sums up the whole series in one moment, and it wouldn’t be the only time the show asked the question so bluntly.

34. “Lady Lazarus” (Season 5, Episode 8)

Written by Matthew Weiner; directed by Phil Abraham.

This episode would be great if only for the ending where Don listens to the Beatles’ “Tomorrow Only Knows” and turns it off halfway through, not liking the sound of the future that it represents. The rest of the episode is pretty great too. Even though Alexis Bledel is one of the weakest actresses to guest star on the series, the plotline where she is Pete’s mistress is a strong element of the show’s fifth season, showcasing Pete’s pathetic tendencies while also revealing the elemental desires that drive him to make such mistakes. Also, this episode marks the point where Megan abandons copywriting. The fracturing of the relationship between Megan and Don that would follow this was just a matter of entropy then.

This episode has the moment where Harry Crane and Jane Siegel sneak into Cooper’s office to look at his new painting, but the standout scene is Sal inviting Ken over to dinner and fawning over him while his wife watches from the sidelines. Ken’s earnest thankfulness, foreshadowing the loving father and husband that he’d become, mixed with Sal’s barely hidden affection for Ken makes this episode another heartbreaking entry in the story of Salvatore Romano.

32. “Field Trip” (Season 7, Episode 3)

Written by Heather Jeng Bladt and Matthew Weiner; directed by Christopher Manley.

The subplot with Betty going on a field trip to a farm with Bobby gives the episode its title, but we all know the title really refers to Don’s first trip back to SC&P after being let go. After cornering Roger and demanding a return date, Don shows up at the office, but Roger’s nowhere in sight. At first scared into retreat, it’s only Ginsberg’s welcoming hello that lures Don back inside. Don Draper has never been more humbled than he is in this episode and the fact that he doesn’t fight it is a ray of hope in the series. After six seasons of Don constantly revisiting his loathsome behaviour, it was refreshing to see him embrace the light for a change.

31. “Tomorrowland” (Season 4, Episode 13)

Written by Jonathan Igla and Matthew Weiner; directed by Matthew Weiner.

Many viewers thought that Dr. Faye Miller might by the woman Don would marry but it ended up being Megan Calvet. In retrospect, this makes perfect sense as Don pursues women for the fresh start they represent, not the impressive individuals they already are. Still, that didn’t take away the thrill of Don taking Megan along as his kids’ babysitter to Disneyland and ending up proposing to her with Anna Draper’s ring. It signaled a huge potential change for the character and a ray of hope at the end of a season fixated on Don’s personal failings. It doesn’t matter that the hope was false. This episode still plays as optimistic, a promise of a future that’ll never be, just as its title suggests.

Mad Men Shoot

30. “Shoot” (Season 1, Episode 9)

Written by Chris Provenzano and Matthew Weiner; directed by Paul Feig.

In the early seasons, Betty was my favourite character on the show. This episode is a large part of why. When the president of McCann Erickson tries to court Don to come work for him, he uses Betty as part of his hiring campaign, offering her model work on a Coca-Cola advertisement that’s meant to help persuade him. Betty, still trying to be the optimistic wife, takes the offer at face value and tries to rediscover some of the joys of her pre-married life. Of course, things don’t go according to plan. Betty is a victim of the world she lives in, the parents who raised her and the husband she married. She believes in the suburban vision even if that vision holds her as a hostage. Over the course of this episode, she starts to sense that the promises told her her whole life have been lies. The final shots where she takes out the pellet gun and unloads on her neighbour’s doves are a beautiful encapsulation of her frustration and anger.

This is the episode that permanently hooked me on Mad Men. It has a few important moments, namely Freddy Rumsen noticing that Peggy has an eye for phrases and getting her to write copy for Belle Jolie lipstick. But it’s the haunting ending, where Don goes to the Gaslight Cafe with his mistress and her beatnik friends and listens to a song version of Psalm 137. I was completely sold on this mysterious show that could entrance me with a song and a man being moved to contemplation by ancient words.

28. “Public Relations” (Season 4, Episode 1)

Written by Matthew Weiner; directed by Phil Abraham.

This episode is flashy as hell, much like the new offices of Sterling Cooper Draper Pryce. While the episode is very much a table-setting episode like most season premieres, it stays focused on its opening question, “Who is Donald Draper?” We see the new offices of the agency Don, Roger, Cooper, Lane, and Pete built at the end of “Close the Door. Have a Seat.” and we see that Don’s life post-Betty is full of hookers and booze. But we also see the Don Draper that imagines himself a frontier man, a cowboy, a vision of what the whole world wants to be. At the end of the episode he sits down with the reporter from the Wall Street Journal and tells him the story he failed to tell the New York Times journalist: about a man with a vision and the guts to execute it. It’s the story Don’s been telling about himself his whole life, with himself as the main audience member.

27. “Maidenform” (Season 2, Episode 6)

Written by Matthew Weiner; directed by Phil Abraham.

Duck Phillips wasn’t a character who garnered much sympathy, but this episode did a great job of showing us why he became the character he is. It explores his alcoholism, his broken family, his desire to please and his desire to build something substantial at Sterling Cooper. It also shows how Duck is a person never destined to get anything of what he wants. He abandons his dreams, his hopes, like he abandons his dog. The scene where takes his beautiful Irish setter, Chauncey, and forces him into the cold New York City streets is heartbreaking.

26. “New Amsterdam” (Season 1, Episode 4)

Written by Lisa Albert; directed by Tim Hunter.

Pete Campbell is a weasel but this episode lets you know why he is. We meet his new wife Trudy and his ungrateful father and his overbearing in-laws. We see how he comes from a family of means and wants to be a creative director like Don but we also see how he can never get what he wants, like money from his father to buy a nice apartment or the chance to pitch his own idea with the accounts he represents like Bethlehem Steel. Pete Campbell is not easy to like, but because of this episode, he’s impossible not to sympathize with.

25. “My Old Kentucky Home” (Season 3, Episode 3)

Written by Dahvi Waller and Matthew Weiner.

Roger hosts a Kentucky Derby soiree as a means to show off his new wife, Jane. He sings a song in blackface, which is horribly offensive but none of his guests seem to mind, aside from Don and Pete. Pete and Trudy dance the Charleston, which is magnificent to behold. Betty meets Henry Francis for the first time. Don bumps into Conrad Hilton without knowing that it’s Conrad Hilton. This episode lays the groundwork for the exceptional run of season three and it does so with maximum pleasure.

24. “For Immediate Release” (Season 6, Episode 6)

Written by Matthew Weiner; directed by Jennifer Getzinger.

This episode is “Shut the Door. Have a Seat.” in a minor chord. It’s another example of Don facing a losing battle, changing the conversation, and walking away with more than he could have dreamed of going in. When going to pitch Chevy, Don bumps into Ted Chaough and convinces him to merge their companies, creating an agency that Chevy would actually respect enough to give its business to. It’s a crazy gamble that works and it’s a great episode to watch. Don’s creativity is one of the chief pleasures of this show, and this episode revels in it.

23. “At the Codfish Ball” (Season 5, Episode 7)

Written by Jonathan Igla; directed by Michael Uppendahl.

Megan’s parents come to visit while Don is up for an award. Sally decides to visit and the happy evening where the family is meant to be celebrating the success of everyone involved turns into a desolate occasion of sad individuals. Sally’s final line in the episode where Glen asks her how the city is and she replies, “Dirty.” captures everything that needs to be said about children discovering the disillusionment of adulthood. She sees her dad in a nice suit accepting an award, but when she realizes he’s not happy and that none of the people he’s with are happy either, her childhood begins to break.

22. “The Mountain King” (Season 2, Episode 12)

Written by Matthew Weiner & Robin Veith; directed by Alan Taylor.

This is the episode where we learn about Don’s relationship with Anna Draper, the wife of the man he stole his identity from. After fleeing the European nomads, Don visits Anna and stays with her while thinking things over about home. Don Draper isn’t a character known for a having a soft side, but if he does have one, this is it. Seeing Don so vulnerable, so open, so genuinely affectionate for another person is surprising and profoundly touching. Also, this is the episode with the horrific rape scene between Joan and her fiance Greg in Don’s office.

21. “Chinese Wall” (Season 4, Episode 12)

Written by Erin Levy; directed by Phil Abraham.

Another episode riffing on what made the season three finale so successful. After Lucky Strike pulls its business from SCDP, the partners scramble to keep the business afloat as they begin to hemorrhage clients who believe that the agency’s demise is inevitable. “Chinese Wall” is a perfect demonstration of how good the characters are at their jobs, as they’re painted into a corner and fight their way to survive.

Mad Men The Phantom

20. “The Phantom” (Season 5, Episode 13)

Written by Jonathan Igla and Matthew Weiner; directed by Matthew Weiner.

The ending of this episode is maybe the best ending ever, as Don walks away from Megan’s commercial set to the tune of Nancy Sinatra’s “You Only Live Twice.” It works as a perfect theme song for Don Draper and the moment solidifies that Don only likes the beginning of things. As the woman sits down next to Don and asks him if he’s alone, we don’t need to hear the answer. We already know what kind of man Don Draper is and what he does in situations like that. What comes before that ending is also stunning, if less iconic, focusing on Don’s guilt regarding Lane’s death and how it reminds him of his dead brother, Adam.

19. “Waldorf Stories” (Season 4, Episode 6)

Written by Brett Johnson and Matthew Weiner; directed by Scott Hornbacher.

This episode cuts back and forth between Don’s drunken whirlwind weekend where he accepts a Clio and flashbacks to how Roger Sterling discovered him in the first place, working as a fur coat salesman who also wrote copy for the store’s advertisements. It shows that even though Don has turned himself into the uber American man, he’ll still always be that poor salesman who forced his way into the world of the rich man he admires. Also, Don’s drunken pitch to Life cereal is a classic: “Enjoy your life...cereal!”

18. “Signal 30” (Season 5, Episode 5)

Written by Frank Pierson and Matthew Weiner; directed by John Slattery.

Lane Pryce punches out Pete Campbell. That’s all this episode needs to stand out. That it does more than supremely entertain is another testament to how good Mad Men is at mixing business with pleasure, depth with entertainment. I always loved Lane Pryce as a character and this episode is one of his standouts, showing his rabid desire to be an American, to fit in with his colleagues and be the kind of important, confident man he so admires. Lane was one of the few characters on the show who was a genuine gentleman, and this episode, which signals the beginning of his decline, is great for how it depicts the confounding of a good man.

17. “Guy Walks Into an Advertising Agency” (Season 3, Episode 6)

Written by Robin Veith and Matthew Weiner; directed by Lesli Linka Glatter.

All anyone remembers is the lawnmower accident, where the new CFO and PPL liaison gets his foot cut off by a lawnmower in a drunken accident at an office party. Mad Men didn’t often use violence, but when it did, it used it in brutally funny ways, this being the series’ highlight. It’s also a great episode depicting how small, dumb decisions can have radical influences on people’s lives, as the accident at the party changes the course of Lane’s career and sets in motion PPL’s eventual move to sell Sterling Cooper.

16. “Meditations in an Emergency” (Season 2, Episode 13)

Written by Matthew Weiner & Kater Gordon; directed by Matthew Weiner.

Betty and Don’s marriage is on the rocks in the midst of the Cuban Missile Crisis. Everyone is scared that their lives might end at any second. Living 50 years after the Cuban Missile Crisis, it’s hard to comprehend that most of the western world feared that nuclear war was inevitable, but this episode puts modern viewers into that iconic historical incident, allowing us to understand how the looming doom of this crisis flavoured every aspect of daily life. This episode also has Betty’s one stunning moment of adultery, where she meets a stranger in a bar and has sex with him in the back room. It’s the culmination of Betty’s marital frustrations, and more thrilling than the PPL takeover of Sterling Cooper that drives the majority of the episode’s narrative.

15. “The Strategy” (Season 7, Episode 6)

Written by Semi Chellas; directed by Phil Abraham.

“The Strategy” marks Don Draper learning to help Peggy instead of hurt her, to work with her instead of boss her, to embrace her as a person he cares about instead of just a coworker he’s fond of. The slow dance that Don and Peggy share to Frank Sinatra’s “My Way” is a beautiful moment that captures their relationship at its best. This episode also shows the other side to their relationship with Peggy’s bitterness at Don’s constant undermining of her work and Don’s dry amusement at Peggy’s insecurities. And the final scene, where the central family of Mad Men, Don, Peggy, and Pete, sit down for dinner at Burger Chef could have been a fitting conclusion for the entire series.

14. “The Arrangements” (Season 3, Episode 4)

Written by Andrew Colville and Matthew Weiner; directed by Michael Uppendahl.

This episode isn’t a big event episode, but for one of the series’ small episodes, it has huge resonance. After Grandpa Gene comes to live with the Drapers, he eventually dies of a stroke while at the grocery store. Betty and Sally find out when a police officer shows up on their doorstep where Sally’s been waiting for Grandpa Gene. It’s heartbreaking to witness Sally and Betty distraught at the news of Gene’s death, but it’s all the moments that precede that ending that are most touching: Sally reading The Decline and Fall of the Roman Empire to Gene in bed, Gene showing off his war trophies to Bobby, Gene letting Sally drive the car down the block. This episode captures the notion of the North American grandparent better than almost any TV episode I can think of.

13. “The Other Woman” (Season 5, Episode 11)

Written by Semi Chellas and Matthew Weiner; directed by Phil Abraham.

This episode where Joan agrees to sleep with a Jaguar executive in order to assure SCDP lands their business is the one where the phrase that Madison Avenue is a whorehouse is made literal. It shows the nasty side of every one of its central characters, even Lane, who views Joan’s accepting of the offer as an inevitability and uses it to plant seeds of partnership in her mind. It’s also the episode where Peggy quits SCDP after Don literally throws money in her face to assuage her creative complaints. Every time Peggy and Don touch hands, it signals an important moment in the series, and here, where Don cradles Peggy’s hand and kisses it, is heartbreaking in its desperation.

12. “In Care Of” (Season 6, Episode 13)

Written by Carly Wray and Matthew Weiner; directed by Matthew Weiner.

Don Draper bottoms out when he reveals the truth of his adolescence growing up in a whorehouse in the midst of a pitch to Hershey’s chocolate. What’s surprising about this episode isn’t that Ted and Peggy finally consummate their flirtation or that Ted and Pete decide to move to California, nor even that the partners force Don out of the agency. It’s that Don decides to be open about his destitute past in such a public and self-destructive way. There’s more feeling, more unclouded emotion in Don’s pitch to Hershey’s than he displays at almost any moment in the series’ entire run.

11. “The Good News” (Season 4, Episode 3)

Written by Jonathan Abrahams and Matthew Weiner; directed by Jennifer Getzinger.

Don visits California and finds out that Anna is dying of cancer. When he returns back home to New York, him and Lane hit the town on New Year’s. This episode shouldn’t be as great as it is, as it mostly follows Don’s idylls at home and abroad. However, its moments of grace are many, and it skirts back and forth between comedy and drama better than any other episode in the series. There’s the scene of Don painting Anna’s wall and signing their names at the bottom, which touches the heart, but there’s also Lane holding the porterhouse steak to his crotch and yelling “Yee-haw” or his observations on the Godzilla movie that he sees with Don: “This film is very good!” The entire episode is a delight.

Mad Men The Doorway

10-9. “The Doorway” (Season 6, Episodes 1 & 2)

Written by Matthew Weiner; directed by Scott Hornbacher.

I wasn’t a huge fan of this episode the first time I watched it, but revisiting it was immensely rewarding. This season premiere acts as a great movie, full of haunting death imagery and elliptical editing that made countless viewers wonder whether Don dies during its runtime. The majority of the plot follows Don and Megan’s trip to Hawaii and Betty’s search in Greenwich Village for a girl who was staying with her and Henry for the holidays. However, the best two moments of the episode come courtesy of Roger Sterling. First, when at his mother’s funeral, Roger cries out, “This is my funeral!” before kicking everyone out, and second, when he cries over the death of his shoeshiner, the tears that had eluded him at his mother’s death finally coming. Ever since Roger had a heart attack in “Long Weekend,” he’s been obsessed with death. “The Doorway” drives home his, and the entire series’, fascination with morbidity like no other.

8. “The Wheel” (Season 1, Episode 13)

Written by Matthew Weiner and Robin Veith; directed by Matthew Weiner.

This episode has the Kodak Carousel pitch. It’s the defining moment of the series, encapsulating Don’s belief in an American mode of life that he’s never experienced, and that likely never existed. His speech on nostalgia set to pictures of his life with Betty and his children, pictures that we never see taken and seem to represent a different man’s life, says all we ever need to know about why Don Draper pursues the things he does or why he chose advertising as his arena of influence. Every pitch that followed in the series was some variation on this one. This episode would be higher on this list if only Peggy’s surprise baby subplot didn’t seem incredulous, even for a show that skirts with soap opera melodrama as much as Mad Men does.

The underlings of Sterling Cooper pull an all-nighter during the election between Richard Nixon and John F. Kennedy, getting drunk and trashing the office. Don Draper’s past in the army is revealed and we find out how he went from being Dick Whitman to Donald Draper. This episode is excellent for enrichening the backgrounds of every character on the show. Not only is Don’s past finally clarified, but we learn about characters like Paul and Joan who seemed one-dimensional until this point. Also, it marks the moment where Pete plays his hand against Don Draper and Bert Cooper kills his power play with one pithy line, “Mr. Campbell, who cares?”

6. “Far Away Places” (Season 5, Episode 6)

Written by Semi Chellas and Matthew Weiner; directed by Scott Hornbacher.

The most formally audacious episode Mad Men has ever made. We experience one day in the lives of Roger, Peggy, and Don, but instead of intercutting between the three, “Far Away Places” depicts one in its entirety before cutting back and moving onto the next, departing from the same moment in the offices of SCDP when Roger tells Don about the upcoming pitch to Howard Johnson’s. What follows should be happy for all the characters involved, but it ends up changing their lives in irreparable ways. After a fight with Abe, Peggy goes to the movies and gives a stranger a handjob, essentially marking the end of her relationship with Abe, even if it took another season for them to finally break up. Roger does LSD and calmly ends his marriage with Jane. Don goes to Howard Johnson’s with Megan for a respite but ends up having the first major fight of his marriage. This episode marks a turning point for all these characters and is one of the series’ best examples of how each character feels like an outsider in the world they inhabit.

5. “Waterloo” (Season 7, Episode 7)

Written by Carly Wray and Matthew Weiner; directed by Matthew Weiner.

This episode is very heavy on plot, but framing the multiple narratives around the Moon Landing grounds it in a way that few other episodes manage. As Jim Cutler’s’ about to force Don out of the company, Roger sets up a sale of the company to McCann Erickson. Peggy makes the pitch to Burger Chef instead of Don, giving the series’ best pitch aside from Don’s Kodak pitch in “The Wheel.” Bert Cooper dies while watching the moon landing. This episode shuffles the deck and deals the cards in a surprising way, setting up for a potentially fascinating final half-season of episodes. However, what’s most surprising is the episode’s final moments where Don has a vision of Bert Cooper giving him some final advice, singing and dancing “The Best Things in Life Are Free.” It’s the best moment of surrealism in the entire series and profoundly moving, despite how silly it is.

The most tragic episode in the series’ run and the most dramatically ironic. Lane kills himself after Don discovers he embezzled funds from the company to pay back his taxes. That the one good man among the partners of SCDP goes down in such a shameful way is devastating, but most devastating is the episode’s small moments of gallows humour. When Lane’s wife buys him a Jaguar as a surprise present, he tries to kill himself in it, putting a hose in the exhaust and flooding the car with carbon monoxide. However, the car won’t start, as the Jaguar is notorious for being a finicky vehicle. It’s only after this failure that he heads to the office and hangs himself. The sight of Lane’s deceased body hanging from the ceiling is horrifying, the show’s most shocking visual, and the saddest moment in a series of many sad moments.

3. “The Suitcase” (Season 4, Episode 7)

Written by Matthew Weiner; directed by Jennifer Getzinger.

Many people would probably list this as the best Mad Men episode and rightly so. It almost exclusively follows Don and Peggy on Peggy’s birthday as they work to come up with the right pitch for Samsonite luggage the night of the Sonny Liston/Muhammad Ali fight. It also has Don avoiding the news of Anna Draper’s death by taking out his frustrations on Peggy, until he’s powerless to hold back his emotions and he breaks down into tears on her lap. Mad Men was a series built around the enigma of Don Draper, his mysterious charm and his dramatic allure. It’s strange then, that the most moving moment in its entire run is seeing behind the curtain and witnessing Don with no defenses, crying his eyes out. It’s the one moment in the show where Don is being completely honest.

2. “The Grown-Ups” (Season 3, Episode 12)

Written by Brett Johnson and Matthew Weiner; directed by Barbet Schroeder.

So much of Mad Men’s appeal had to do with its transporting the viewer back to the 1960s. Its clothing, its casual drinking, its impeccable style was a constant delight over the series’ run. No episode transported the viewer to the past as well as this episode, where everyone grapples with the assassination of JFK. Roger’s daughter, Margaret, gets married but the wedding is half empty as the country goes into mourning. Betty tries to console her children, but she’s as confused as they are, pondering what kind of world they live in where their president can be killed driving down the street. The episode climaxes with Betty telling Don that she no longer loves him, driving home the episode’s funereal tone. It’s the most transporting the series ever got, sending us back in time to experience a foundational moment in American history, but also allowing us to comprehend the disenchantment and sadness of the people who experienced the crisis in real time.

Mad Men Shut the Door Have a Seat

1. “Shut the Door. Have a Seat.” (Season 3, Episode 13)

Written by Matthew Weiner & Erin Levy; directed by Matthew Weiner.

This episode shows Don Draper at his best and his worst. Most people remember the episode for Don’s scheme to form a new agency when PPL plans to sell Sterling Cooper to McCann Erickson. This narrative line is the most thrilling the series ever got, as exciting as any episode of Breaking Bad. It’s practically a heist movie as Don, Roger, Cooper, and Lane gather their small team of employees to start a new agency and steal the files for their clients over the weekend before the agency is sold. The plotline ended up radically changing the setting of Mad Men, jettisoning characters like Paul Kinsey and forcing the people behind the series to contemplate just who and what is essential to the show, just as the characters are forced to confront who is essential to their new agency. But this episode also marks the end of Don and Betty’s marriage, and Don’s arguably lowest point, where he becomes physically violent with Betty after learning of her plans to marry Henry Francis. Don is brilliant enough to conceive and execute the plan to leave Sterling Cooper and form Sterling Cooper Draper Pryce, but he’s also monster enough to threaten to destroy his wife when he finds out she is in love with a new man. For displaying Mad Men at its most thrilling and its most introspective, for being a heist film and a domestic drama, for radically upending the show’s status quo and bringing Don Draper down to hell at the same time as he summits Olympus, “Shut the Door. Have a Seat.” is the best episode Mad Men ever produced.